Aza-Annulation Chemistry

The aza-annulation reaction serves as a powerful tool for synthetic organic chemists due to its simplicity and the ability to rapidly increase molecular complexity in a single step, utilizing readily available starting materials. Furthermore, the potential for further modifications through the functional groups present in the aza-annulation products enhances its utility. This annulation methodology facilitates the construction of 5- and 6-membered nitrogen heterocycles from simple enamines, which are generated by the condensation of β-ketoesters and primary amines. The subsequent Michael addition with maleic or itaconic anhydrides, followed by intramolecular acylation, enables formal [3+2] and [3+3] annulations that form new C-C and C-N bonds. The resulting annulation products feature two newly created stereocenters along with enamide, carboxylic acid, lactam, and ester functional groups, which can be further diversified to develop next-generation building blocks.

Synthetic Organic Electrochemistry 

Organic electrochemistry is one of the oldest branches of chemical science, with numerous impressive achievements, many of which have been successfully industrialized. However, its potential as a synthetic tool has long been underestimated. In recent years, interest in electrochemical methods among synthetic chemists has surged dramatically.

Our recent and ongoing research in this area focuses on the oxidative activation of aromatic compounds, followed by the capture of highly reactive cation radicals with suitable nucleophiles. The mechanistic pathway is outlined below. Initially, a one-electron oxidation generates a cation radical, which is then intercepted by a nucleophile, leading to the formation of a cyclohexadienyl radical. The desired product is subsequently obtained through a second one-electron oxidation followed by a deprotonation step.